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There was never any doubt Ryan Dempster would be a success, no matter that he elected to do. Always a jokester, an aficionado of clubhouse pranks, he was the pitcher in the wry during a 16-year career that began with the 108-loss Marlins in 1998 and ended with a World Series ring with the Red Sox in 2013. He knew how to keep the game fun and make it sound that way, so he has been a natural on the MLB Network the past year during a sabbatical while mullling whether to continue playing. But Dempster threw his final curve just over a week ago when he made it official he was done as a pitcher and the Cubs announced he would join the front office of his former team as a special...

Related "Jon Lester" Articles

There was never any doubt Ryan Dempster would be a success, no matter that he elected to do.
Always a jokester, an aficionado of clubhouse pranks, he was the pitcher in the wry during a 16-year career that began with the 108-loss Marlins in 1998 and...

The Miami Marlins were busy talking but deals were elusive on the first day of the baseball Winter Meetings.
The only net result was the subtraction of former starting catcher Rob Brantly, who was claimed on waivers by the Chicago White Sox.
The Marlins...

As the major league free-agency sweepstakes heat up this week, the Miami Marlins are not among the shoppers in a rush to reel in any of the prominent names on the market.
Michael Hill, the Marlins' president of baseball operations, made it clear...

MIAMI When Jarred Cosart faced them Saturday at Minute Maid Park his name was among many on a "laundry list" of controllable starters the Marlins found intriguing.
At the time, President of Baseball Operations Michael Hill did not foresee...

1. For now, it's just lawyer-on-lawyer hate. But the question for the Pouncey brothers, Mike and Maurkice, as well as their respective teams, the Dolphins and Steelers is whether an incident at a South Beach nightclub becomes something more, as the lawyer...

MIAMI The Marlins' preference is to add a controllable starter before Thursday afternoon's non-waiver trade deadline. That hasn't precluded them from entertaining a rental – specifically Red Sox left-hander Jon Lester.
The demand is such that the Red Sox...

Billy Beane knows the Yoenis Cespedes question is coming, because it's always looming when you talk about the A's these days. This is seven months after the A's general manager controversially dealt Cespedes for pending free agent ace Jon Lester,...

MESA, Ariz. — Jon Lester changed leagues, uniform colors and spring training venues.
But the confidence Lester developed over nine seasons with the Red Sox remains strong as he seeks to help the Cubs win a World Series for the first time in 107 seasons....

MESA, Ariz. — The Cubs begin preparation for the 2015 season Friday, but they also hope to begin to a lay a foundation for long-term success when they conduct their first workout for pitchers and catchers under new manager Joe Maddon.
With the core of...

Before the San Francisco Giants enjoyed their third parade in five years, before a Chevrolet executive memorably advised World Series most valuable player Madison Bumgarner he had won a truck equipped with "technology and stuff," before the...

Max Scherzer and Jon Lester might as well have neon-green dollar signs stamped all over their uniforms and caps when spring training opens next week.
Their careers were redefined this offseason when they joined baseball's elite echelon of $100 million...

As a youngster in his native Venezuela, Miguel Montero received instruction on fielding grounders from 11-time Gold Glove shortstop Omar Vizquel.
"I remember him telling us to keep our hands soft," Montero recalled of the clinic. "Keep...

Whether the Cubs or White Sox won the offseason is really a determination that should be made as their moves play out on the field, but there's little doubt the teams at least won the attention of the baseball world.
The clubs posted identical 73-89...

James Shields remains the biggest free agent on the market as spring training approaches, and Cubs manager Joe Maddon, for one, thinks the right-hander would be "a nice prize" to win.
Maddon told the MLB Network Radio show "Inside...

Red Sox general manager Ben Cherington is pretty much done adding for this offseason. "I would expect the group we have for spring training is in place," he said Thursday after the Red Sox announced a $19.25 million, three-year contract with...

Yes, the Giants' announcements about signing Nori Aoki and re-signing Ryan Vogelsong were slightly less than the transformative additions that Giants fans have been craving all winter. And that came after the acquisition of third baseman Casey McGehee...

SAN DIEGO — The Red Sox entered baseball's winter meetings in search of three starting pitchers. It appears they may have reached their goal.Hours after acquiring one starting pitcher in Arizona's Wade Miley, the Boston Red Sox unloaded outfielder...

SAN DIEGO — When I approached Jon Lester at the All-Star Game in Minneapolis five months ago and asked him about the possibility of coming to the Cubs as a free agent, he raised his eyebrows and shouted out for help.
"I got my first destination...

1. He is a cancer survivor. In 2006, he suffered a sore back and was put on the disabled list. Soon thereafter he was diagnosed with non-Hodgkin lymphona. After treatment he is now cancer free. In 2012, he started the NVRQT Campaign to support...

To Tyler Christofferson, Jon Lester always will be the Little League teammate who wore his hat backward and No. 24 jersey like hero Ken Griffey Jr. did, the grade-school buddy who matured into a better person than player even though he's a major league...